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(11) | EP 0 107 008 B1 |
| (12) | EUROPEAN PATENT SPECIFICATION |
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| (54) |
9,10-bis(phenylethynyl)-anthracenes 9,10-Bis-(phenyläthinyl)-anthracene Bis(phényléthinyl)-9,10 anthracènes |
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| Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). |
[0001] The invention, described herein, was made in the performance of work supported by the Office of Naval Research (Contract No. N-00014-77-C-0634), and is subject to the provisions of ASPR 7-104.18, December 1969, and ASPR 7-302.23 (b) long form, August 1977.
[0002] The invention relates to novel fluorescer compounds, to mixtures containing those compounds which are useful for generating chemiluminescence, and to the use of such mixtures for generating chemiluminescence.
[0003] Zweig and Maulding, in U.S. Patents Nos. 3,557,233 and 3,729,426, and Maulding, in U.S. Patent No. 3,888,786 described 9,1-bis(phenylethynyl)anthracenes substituted by chloro, bromo, fluoro, or lower alkyl groups and their use as fluorescers with certain oxalic-type compounds which react with peroxide to produce chemiluminescence.
[0004] Arthen and Manfre, in U.S. Patent Application Serial No. 341,390, filed January 21,1982, describe 9,10- bis (C4-C22 alkylphenylethynyl)anthracenes, mixtures containing such compounds, and the use of such mixtures for generating chemiluminescence.
[0005] The invention provides fluorescers for chemiluminescent mixtures that will have higher chemiluminescence efficiencies as measured by the quantum yield, and will have higher light output as measured by the light capacity, than those described by Zweig and Maulding.
[0006] The invention provides fluorescers for chemiluminescent mixtures that have slightly lower light capacities and quantum yields than those described by Arthen and Manfre. However, the fluorescers of this invention are more readily soluble in polar organic solvents, such as dimethyl phthalate, diethyl ether, tetrahydrofuran, and ethyl acetate, than the fluorescers of Arthen and Manfre.
Summary of the Invention
[0007] The invention provides novel fluorescer compounds having the formula (I),
wherein R is selected from the group consisting of C, to C, alkyl, C4 to C8 cycloalkyl, and C3 to C6 alkenyl.
[0008] Compounds of formula (I) can be prepared by reacting about two molecular proportions of the corresponding lithium phenylacetylide with anthraquinone to obtain a 9,10-dihydro-9,10-dihydroxy-9,10- bis(phenylethynyl)anthracene 'and converting the latter to the corresponding 9,10-bis(phenylethynyl)-anthracene by methods described by Maulding in U.S. Patent 3,911,038.
[0009] Illustrated examples of suitable compounds of formula (I) include the following:
9,10-bis[2-[4-(methoxymethyl)phenyl]ethynyl]anthracene,
9,10-bis[2-[4-(n-butoxymethyl)phenyl]ethynyl]anthracene,
9,10-bis[2-[3-(n-octyloxymethyl)phenyl]ethynyl]anthracene,
9,10-bis[2-[4-(cyclohexyloxymethyl)phenyl]ethynyl]anthracene,
9,10-bis[2-[4-(allyloxymethyl)phenyl]ethynyl]anthracene,
9,10-bis[2-[4-(methallyloxymethyl)phenyl]ethynyl]anthracene,
[0010] The compositions of formula (I) may comprise mixtures of isomers substituted at the 3 and 4 positions of the phenyl moiety.
[0011] The term "chemiluminescence," as employed herein, is defined as the generation of electromagnetic radiation between about 300 and 1200 nanometers by means of a chemical reaction.
[0012] The term "chemiluminescent reactant" is defined as any compound which enters into a chemical reaction with a peroxide component to produce chemiluminescence. The preferred chemiluminescent reactants for use in this invention are oxalic acid esters, and certain oxamides which are described for example in U.S. Patents Nos. 3,597,362, 3,888,786, and 4,226,738.
[0013] The term "composition for reaction with a peroxide component to generate chemiluminescence," as employed herein, is defined as a mixture of a compound of formula (I) and a chemiluminescent reactant in a diluent in concentrations sufficient to produce chemiluminescence by admixing with a peroxide component. Thus, the initial concentrations of the compound of formula (I), the reactant compound, and the ingredients of the peroxide component in the reaction mixture must be sufficient to produce chemiluminescence.
[0014] The term "admixing," as used herein, means "reacting" or sufficiently bringing together component reactants to obtain chemiluminescence.
[0015] The fluorescer compound of formula (I) must not readily react with the peroxide component used in this invention, or with the reactant compound, and must be at least partially soluble in the diluent employed.
[0016] The composition for reaction with a peroxide component to generate chemiluminescence may comprise a liquid which will solubilize the fluorescer compound of formula (I) and the reactant compound to provide initial concentrations in the reacting system of about 10-3M to about 10M, preferably about 10-1 M to about 1 M, of the reactant compound and about 10-5M to about 10-1 M, preferably about 10-3M to 10-2M, of the fluorescer compound. This liquid diluent must be relatively unreactive toward the other ingredients of the chemiluminescent mixture.
[0017] The molar concentrations of the reactant compound, and the fluorescer compound in the composition before addition and reaction with the peroxide component is about 1.1-2.5, preferably about 1.2-1.3, times the molar concentrations of the same materials in the reacting system described above.
[0018] Typical diluents which can be used in the composition for reaction with a peroxide component include esters, ethers, aromatic hydrocarbons, chlorinated aliphatic and aromatic hydrocarbons such as those described for the use in U.S. Patents 3,749,679 and 3,888,786. The most preferred diluent is dibutyl phthalate. Solvent combinations may be used but such combinations should not include strongly electron donating solvents, strongly acidic, or strongly basic solvents.
[0019] The term "diluent," as used herein, is defined as a liquid solvent, or vehicle, for the compound of formula (I) and the reactant compound.
[0020] The term "peroxide component," as used herein, means a solution of a hydrogen peroxide compound, a hydroperoxide compound, or a peroxide compound in a suitable diluent.
[0021] The term "hydroperoxide compound" includes (1) hydrogen peroxide and (2) hydrogen peroxide- producing compounds.
[0022] Hydrogen peroxide is the preferred hydroperoxide compound and may be employed as a solution of hydrogen peroxide in a solvent or as an anhydrous hydrogen peroxide compound such as sodium perborate, sodium peroxide, and the like. Whenever hydrogen peroxide is contemplated to be employed, any suitable compound may be substituted which will produce hydrogen peroxide.
[0023] ' Diluents which can be employed for the peroxide component include any liquid which is relatively unreactive toward the hydroperoxide, the chemiluminescent reactant, and the fluorescer compound, and which accommodates a solubility to provide at least 0.01 M hydroperoxide solution. Solvents suitable as diluents for the hydroperoxide component include water; alcohols, such as diethyl ether, diamyl ether, tetrahydrofuran, dioxane, dibutyldiethyleneglycol, perfluoropropyl ether, and 1,2-di-methoxyethane; and esters, such as ethyl acetate, ethyl benzoate, dimethyl phthalate, dioctylphthalate, propyl formate. Solvent combinations can, of course, be used such as combinations of the above with anisole, tetralin, and chlorobenzene, providing said solvent combination accommodates hydroperoxide solubility. However, strong electron donor solvents such as dimethyl formamide, dimethyl sulfoxide, and hexamethylphosphoramide should not, in general, be used as a major diluent for the peroxide component.
[0024] The preferred diluent for the peroxide component is a mixture of about 80 volume percent dimethyl phthalate and about 20 volume percent tertiary butanol.
[0025] The hydrogen peroxide concentration in the peroxide component may range from about 0.2M to about 15M. Preferably, the concentration ranges from about 1 M to about 2M.
[0026] The lifetime and intensity of the chemiluminescent light emitted can be regulated by the use of certain regulators such as:
(1) by the addition of a catalyst which changes- the rate of reaction of hydroperoxide with the compound for formula (I). Catalysts which accomplish that objective include those described in M. L. Bender, "Chem. Revs.," Vol. 60, pg. 53 (1960). Also, catalysts which alter the rate of reaction or the rate of chemiluminescence include those accelerators of U.S. Patent No. 3,775,366, and decelerators of U.S. Patent Nos. 3,691,085 and 3,704,231, or
(2) by the variation of hydroperoxide. Both the type and the concentration of hydroperoxide are critical for the purpose of regulation.
[0027] Preferably, a weakly basic accelerator, such as sodium salicylate, is included in the peroxide component to control the lifetime of the chemical lighting system. The concentration of weakly basic accelerator used in the peroxide component may range from about 10-6M to about 10-2M, preferably from about 10-4M to about 10-3M.
[0028] The initial concentration of the ingredients of the peroxide component in the reacting system is about 0.15 to 0.60 of the concentrations in the peroxide component since the peroxide component comprises about 15 to about 60 volume percent of the reaction mixture.
[0029] The concentration of the hydroperoxide compound in the chemiluminescent reaction is at least equal to the molar concentration of the chemiluminescent reactant and is preferably 1.2 to 5.0 times the concentration of the chemiluminescent reactant in the reacting system described above. The optimum concentrations must be determined experimentally for each specific system.
[0030] The following examples are illustrative of the present invention. All parts are by weight unless otherwise indicated.
Example 1
Preparation of a Mixture of 9,10-bis[2-[3-(and 4-) (allyloxymethyl)phenyl]ethynyl]anthracenes
[0031] Lithium amide (1.6 grams; 0.072 mole) and a mixture of 3 (and 4)-(allyloxymethyl)phenylacetylenes (11.4 grams; 0.066 mole) are suspended in dry-dioxane (125 mls) and stirred at reflux temperature, under nitrogen, for 4 hours. The suspension is cooled to 15°C and anthraquinone (6.2 grams; 0.03 mole) is added thereto, along with additional dioxane (50 mls). The resulting mixture is stirred at reflux for 18 hours, and then cooled to room temperature.
[0032] Aqueous acetic acid (9 mls; 50%) is added to the reaction mixture, followed by the addition of a solution of stannous chloride dihydrate (20 grams; 0.09 mole) in N,N-dimethylformamide (80 mls). The resulting solution is stirred at room temperature for 4 hours, and then cooled in an ice bath. Glacial acetic acid (50 mls) and dilute sulfuric acid (50 mis; 5N) are added thereto and the reaction mixture is stirred until the yellow-brown precipitate becomes granular. The solid is then collected by filtration, washed with water, and dried under vacuum at room temperature. The dried solid is dissolved in hot methylcyclohexane, and stirred with Magnesol* (Trademark; FMC Corporation), DARCO° Decolorizing Carbon, (ICI Americas, Inc.), and HYFLOO Super-Cel (Johns-Manville Sales Corporation) at ambient temperature for one hour. The mixture is filtered and the filtrate is cooled to obtain a bright yellow crystalline precipitate, which is recovered by filtration and dried under vacuum, m.p. 55-62°C.
Anal. Calculated for C38H30O2: C, 88.03%, H, 5.79%
Found: C, 88.48%, H, 5.89%
Comparison Example 2
Preparation of a Mixture of 9,10-bis[3(and 4)-(hydroxymethyl)phenylethynyl]anthracene
[0033] To a stirred solution of the product of Example 1 (5.2 grams; 0.01 mole) in dry dioxane (75 mols) is added selenium (IV) dioxide (2.4 grams; 0.022 mole) and glacial acetic acid (1.8 mls; 0.03 mole), under nitrogen. After stirring at reflux temperature for 3) hours, analysis by thin layer chromatography (50/50 methylene chloride: ethyl acetate) reveals almost complete absence of the starting material. The hot solution is filtered to remove a black solid, which is washed with hot dioxane (2 x 50 mls). Evaporation of the filtrate and washings yields an orange semi-solid.
[0034] Elution of this material through a Waters Prep 500.High Performance Liquid Chromatography (2:1 chloroform/tetrahydrofuran) yields the desired compound as the most polar fraction, m.p. 160―169°C.
[0035] The nuclear magnetic resonance and infrared spectra of the product are consistant with the proposed structure.
Examples 3 and 4
Determination of Chemiluminescence
[0036] Solutions of 7.5 mls of bis(6-carbopentoxy-2,4,5-trichlorophenyl)oxalate (CPPO) and selected fluorescers (defined in Table I) are made in dibutyl phthalate. Each solution is mixed with 2.5 mls of a peroxide component which consists of hydrogen peroxide and sodium salicylate in 80% dimethyl phthalate-20% (by volume) tertiary butanol. Each of the chemiluminescent reaction mixtures contains initial concentrations of 0.38 M hydrogen peroxide, 1.56 x 10-4 M sodium salicylate, 0.10M CPPO, and 2.25 x 10-3M of the fluorescer. Quantitative measurements of the chemiluminescence of the solutions are carried out by means of a Hirt-Roberts radiometer-spectrophotometer using the procedure described in the Journal of organic Chemistry, Volume 44, page 4115 (1979). The results are shown in Table I. The fluorescer compounds of Examples 1 and 2 provided significantly higher light capacities and quantum yields than the comparison fluorescer (Example 3 which was selected because it illustrates the criticality of the nature of the R radical in formula (I).
Example 5
Preparation of a Mixture of 9,10-bis[3 (and 4)-(n-butoxymethyl)phenylethynyl]anthracenes
Claims for the following Contracting State(s) : s: BE CH DE FR GB IT LI NL SE
1. Compounds of the formula
wherein R is selected from the group consisting of C1 to C8 alkyl, C4―C8 cycloalkyl and C3―C6 alkenyl.
wherein R is selected from the group consisting of C1 to C8 alkyl, C4―C8 cycloalkyl and C3―C6 alkenyl.
2. A compound according to Claim 1 consisting of 9,10-bis[2-[4-(methoxymethyl)phenyl]ethynyl]-anthracene.
3. A compound according to Claim 1 consisting of 9,10-bis[2-[4-(n-butoxymethyl)phenyl]ethynyl]-anthracene.
4. A compound according to Claim 1 consisting of 9,10-bis[2-[3-(n-octyloxymethyl)phenyl]ethynyl]-anthracene.
5. A compound according to Claim 1 consisting of 9,10-bis[2-[4-(cyclohexyloxymethyl)phenyl]ethynyl]-anthracene.
6. A compound according to Claim 1 consisting of 9,10-bis[2-[4-(allyloxymethyl)phenyl]ethynyl]-anthracene.
7. A compound according to Claim 1 consisting of 9,10-bis[2-[4-(methallyloxymethyl)phenyl]ethynyl]-anthracene.
8. A chemiluminescent mixture comprising a chemiluminescent reactant, a peroxide component
and at least one fluorescent compound having the composition defined by Claim 1.
9. A composition for reaction with a peroxide component to generate chemiluminescence
comprising at least one fluorescent compound defined by Claim 1.
10. A chemiluminescent mixture defined by Claim 8 wherein the fluorescent compounds
consist essentially of 9,10-bis[2-[3- (and 4)-(allyloxymethyl)phenyl]ethynyl]anthracenes.
Claims for the following Contracting State(s) : AT
1. A chemiluminescent mixture comprising a chemiluminescent reactant, a peroxide component
and at least one fluorescent compound of the formula (I)
wherein R is selected from the group consisting of C, to C8 alkyl, C4―C8 cycloalkyl and C3―C6 alkenyl.
wherein R is selected from the group consisting of C, to C8 alkyl, C4―C8 cycloalkyl and C3―C6 alkenyl.
2. A chemiluminescent mixture defined by Claim 1 wherein the fluorescent compounds
consist essentially of 9,10-bis[2-[3 (and 4)-(allyloxymethyl)pheny]ethynyl]anthracenes.
3. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[4-(methoxymethyl)-phenyl]ethynyl]anthracene.
4. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[4-(n-butoxymethyl)-phenyl]ethynyl]anthracene.
5. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[3-(n-octyloxymethyl)-phenyl]ethynyl]anthracene.
6. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[4-(cyclohexyloxy-
methyl)phenyl]ethynyl]anthracene.
• 7. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[4-(allyloxymethyl)-phenyl]ethynyl]anthracene.
8. A mixture defined by Claim 1, wherein the fluorescent compound is 9,10-bis[2-[4-(methallyloxy-
_ methyl)phenyl]ethynyl]anthracene.
9. A composition for reaction with a peroxide component to generate chemiluminescence
comprising at least one fluorescent compound defined by Claim 1.
Patentansprüche für folgende(n) Vertragsstaat(en) : BE CH DE FR GB IT LI NL SE
Verbindungen der Formel
wobei R ausgewählt ist aus der Gruppe bestehend aus C1―C8-Alkyl, C4―C8-Cycloalkyl und C3―C6-Alkenyl.
wobei R ausgewählt ist aus der Gruppe bestehend aus C1―C8-Alkyl, C4―C8-Cycloalkyl und C3―C6-Alkenyl.
2. Verbindung nach Anspruch 1, nämlich 9,10-Bis[2-[4-(methoxymethyl)phenyl]äthinyl]anthracen.
3. Verbindung nach Anspruch 1, nämlich 9,10-Bis[2-[4-(n-butoxymethyl)phenyl]äthinyl]anthracen.
4. Verbindung nach Anspruch 1, nämlich 9,10-Bis[2-[3-(n-octyloxymethyl)phenyl]äthinyl]anthracen.
5. Verbindung nach Anspruch 1, nämlich 9,10-Bis[2-[4-(cyclohexyloxymethyl)phenyl]äthinyl].
anthracen.
6. Verbindung nach Anspruch 1, nämlich 9,10-Bis[2-[4-(allyloxymethyl)phenyl]äthinyl]anthracen.
7. Verbindung nach Anspruch 1', nämlich 9,10-Bis[2-[4-(methallyloxymethyl)phenyl]äthinyl]anthracen.
8. Chemilumineszierendes Gemisch, umfassend einen chemilumineszierenden Reaktanten,
eine Peroxidkomponente und mindestens eine Leuchtstoffverbindung mit der in Anspruch
1 angegebenen Zusammensetzung.
9. Eine Zusammensetzung für die Reaktion mit einer Peroxidkomponente zur Erzeugung
von Chemilumineszenz, umfassend mindestens eine Leuchtstoffverbindung gemäß Anspruch
1.
10. Chemilumineszierendes Gemisch nach Anspruch 8, wobei die Leuchtstoffverbindungen
im wesentlichen aus 9,10-Bis[2-[3 (und 4)-(allyloxymethyl)phenyl]äthinyl]anthracenen
bestehen.
Patentansprüche für folgende(n) Vertragsstaat(en) : AT
1. Ein chemilumineszierendes Gemisch, umfassend einen chemilumineszierenden Reaktanten,
eine Peroxidkomponente und mindestens eine Leuchtstoffverbindung der Formel (I)
wobei R ausgewählt ist aus der Gruppe bestehend aus C1―C8-Alkyl, C4―C8-Cyloakyl und C3―C6-Alkenyl.
wobei R ausgewählt ist aus der Gruppe bestehend aus C1―C8-Alkyl, C4―C8-Cyloakyl und C3―C6-Alkenyl.
2. Ein chemilumineszierendes Gemisch nach Anspruch 1, wobei die Leuchtstoffverbindungen
im wesentlichen aus 9,10-Bis[2-[3 (und 4)-(allyloxymethyl)phenyl]äthinyl]anthracenen
bestehen.
3. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis[2-[4-(methoxymethyl)phenyl]äthinyl]anthracenen
ist.
4. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis[2-[4-(n-butoxymethyl)phenyl]äthinyl]anthracen
ist.
5. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis[2-[3-(n-ocytyioxy-
methyl)phenyl]äthinyl]anthracen ist.
6. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis[2-[4-(cyclohexyloxy-
methyl)phenyl]äthinyl]anthracen ist.
7. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis(2-[4-(allyloxymethyl)phenyl]-äthinyl]anthracen
ist.
8. Mischung nach Anspruch 1, wobei die Leuchtstoffverbindung 9,10-Bis[2-[4-(methallyloxy-
methyl)phenyl]äthinyl]anthracen ist.
9. Eine Zusammensetzung für die Reaktion mit einer Peroxidkomponente zur Erzeugung
von Chemilumineszenz, umfassend mindestens eine Leuchtstoffverbindung gemäß Anspruch
1.
Revendications pour l'(les) Etat(s) contractant(s) suivant(s) : BE CH DE FR GB IT
LI NL SE
1. Composés de formule:
dans laquelle R est choisi parmi les radicaux alkyle en Ci à C8, cycloalkyle en C4 à C8 et alcényle en C3 à C6.
dans laquelle R est choisi parmi les radicaux alkyle en Ci à C8, cycloalkyle en C4 à C8 et alcényle en C3 à C6.
- 2. Composé selon la revendication 1 consistant en 9,10-bis[2-[4-(méthoxyméthyl)phényl]éthynyl]-anthracène.
3. Composé selon la revendication 1 consistant en 9,10-bis[2-[4-(n-butoxyméthyl)phényl]éthynyl]-anthracène.
4. Composé selon la revendication 1 consistant en 9,10-bis[2-[3-(n-octyloxyméthyl)phényl]éthynyl]-anthracène.
5. Composé selon la revendication 1 consistant en 9,10-bis[2-[4-(cyclohexyloxyméthyl)phényl]éthynyl]-anthracène.
6. Composé selon la revendication 1 consistant en 9,10-bis[2-[4-(allyloxyméthyl)phényl]éthynyl]-anthracène.
7. Composé selon la revendication 1 consistant en 9,10-bis[2-[4-(méthallyloxyméthyl)phényl]éthynyl]-anthracène.
8. Mélange chimioluminescent comprenant un réactif chimioluminescent, un composant
peroxyde et au moins un composé fluorescent défini à la revendication 1.
9. Composition destinée à réagir avec un composant peroxyde pour produire de la chimioluminescence
comprenant au moins un composé fluorescent défini à la revendication 1.
10. Mélange chimioluminescent selon la revendication 8 dans lequel les composés fluorescents
consistent essentiellement en 9,10-bis[2-[3(et 4)-(allyloxyméthyl)phényl]éthynyl]anthracènes.
Revendications pour l'(les) Etat(s) contractant(s) suivant(s) : AT
1. Mélange chimioluminescent comprenant un réactif chimioluminescent, un composant
peroxyde et au moins un composé fluorescent de formule:
dans laquelle R est choisi parmi les radicaux alkyle en Ci à Cs, cycloalkyle en C4 à C8 et alcényle en C3 à C6.
dans laquelle R est choisi parmi les radicaux alkyle en Ci à Cs, cycloalkyle en C4 à C8 et alcényle en C3 à C6.
2. Mélange chimioluminescent selon la revendication 1, dans lequel les composés fluorescents
consistent essentiellement en 9,10-bis[2-[3(et 4)-(allyloxyméthyl)phényl]éthynyl]anthracènes.
3. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[4-(méthoxy-
méthyl)phényl]éthynyl]anthracène.
4. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[4-(n-butoxy-
méthyl)phényl]éthynyl]anthracène.
5. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[3-(n-octyloxyméthyl)phényl]éthynyl]anthracène.
6. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[4-(cyclohexyloxyméthyl)phényl]éthynyl]anthracène.
7. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[4-(allyloxy-
méthyl)phényl]éthynyl]anthracène.
8. Mélange selon la revendication 1, dans lequel le composé fluorescent est le 9,10-bis[2-[4-(méthallyloxyméthyl)phényl]éthynyl]anthracène.
9. Composition destinée à réagir avec un composant peroxyde pour produire de la chimioluminescence
comprenant au moins un composé fluorescent défini à la revendication 1.